Rhodium-Catalyzed Aldehyde Arylation via Formate-Mediated Transfer Hydrogenation: Beyond Metallic Reductants in Grignard/Nozaki-Hiyami-Kishi-Type Addition.

Autor: Swyka RA; Department of Chemistry , University of Texas at Austin , Austin , Texas 78712 , United States., Zhang W; Department of Chemistry , University of Texas at Austin , Austin , Texas 78712 , United States., Richardson J; Discovery Chemistry Research and Technologies , Eli Lilly and Company Limited , Erl Wood Manor , Windlesham , Surrey GU20 6PH , United Kingdom., Ruble JC; Discovery Chemistry Research and Technologies , Eli Lilly and Company , Indianapolis , Indiana 46285 , United States., Krische MJ; Department of Chemistry , University of Texas at Austin , Austin , Texas 78712 , United States.
Jazyk: angličtina
Zdroj: Journal of the American Chemical Society [J Am Chem Soc] 2019 Feb 06; Vol. 141 (5), pp. 1828-1832. Date of Electronic Publication: 2019 Jan 29.
DOI: 10.1021/jacs.8b13652
Abstrakt: The first intermolecular carbonyl arylations via transfer hydrogenative reductive coupling are described. Using rhodium catalysts modified by t Bu 2 PMe, sodium formate-mediated reductive coupling of aryl iodides with aldehydes occurs in a chemoselective fashion in the presence of protic functional groups and lower halides. This work expands the emerging paradigm of transfer hydrogenative coupling as an alternative to pre-formed carbanions or metallic reductants in C═X addition.
Databáze: MEDLINE